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Brilliant Mistakes: Finding Success on the Far Side of Failure
Named #1 Best Business Book of 2011, by Patriot-News–PennLive.com
If you have ever flown in an airplane, used electricity from a nuclear power plant, or taken an antibiotic, you have benefited from a brilliant mistake.
Each of these life-changing innovations was the result of many missteps and an occasional brilliant insight that turned a mistake into a surprising portal of discovery. In Brilliant Mistakes, Paul Schoemaker, founder and chairman of Decision Strategies International, shares critical insights on the surprising benefits of making well-chosen mistakes.
Brilliant Mistakes explores why minimizing mistakes may be the greatest mistake of all, situations when mistakes are most beneficial and when they should be avoided, the counter-intuitive idea that we should deliberately permit errors at times, and how to make the most of brilliant mistakes to improve business results.
Brilliant Mistakes is based on solid academic research and insights from Schoemaker’s work with more than 100 organizations, as well as his provocative Harvard Business Review article with Robert Gunther, “The Wisdom of Deliberate Mistakes.” Schoemaker provides a practical roadmap for using mistakes to accelerate learning for your organization and yourself.
If you have ever flown in an airplane, used electricity from a nuclear power plant, or taken an antibiotic, you have benefited from a brilliant mistake.
Each of these life-changing innovations was the result of many missteps and an occasional brilliant insight that turned a mistake into a surprising portal of discovery. In Brilliant Mistakes, Paul Schoemaker, founder and chairman of Decision Strategies International, shares critical insights on the surprising benefits of making well-chosen mistakes.
Brilliant Mistakes explores why minimizing mistakes may be the greatest mistake of all, situations when mistakes are most beneficial and when they should be avoided, the counter-intuitive idea that we should deliberately permit errors at times, and how to make the most of brilliant mistakes to improve business results.
Brilliant Mistakes is based on solid academic research and insights from Schoemaker’s work with more than 100 organizations, as well as his provocative Harvard Business Review article with Robert Gunther, “The Wisdom of Deliberate Mistakes.” Schoemaker provides a practical roadmap for using mistakes to accelerate learning for your organization and yourself.
190 pages, Paperback
First published November 8, 2011
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280 people want to read
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Displaying 1 - 18 of 18 reviews
December 5, 2018
This could have been a great book, and was a great concept, but it just wasn't all that good in implementation.
The basic argument is you should try to falsify your beliefs through texts, try things which will succeed/fail in ways which are independent of mainstream beliefs or the rest of your "portfolio" of ideas and beliefs, etc. One of the key ideas is separating experiments based on the 2 axes of cost of failure and benefit if successful, and to try to take risks/make mistakes/experiment in ways where failure has low cost but high returns if successful.
The good part: it's an introduction to decision theory for people who might actually have real decisions to make (i.e. not just academics studying decision theory...). Lots of practical examples from business, clear presentation, etc.
Downside: Because it can't use normal human language like "local maxima" and mathematical analogies, it's really verbose and imprecise.
Calling likely-to-fail-but-positive-EV experiments "deliberate mistakes" or failures is a stretch, but it's the hook for the book, so he repeats it a lot.
Overall, this is a decent book for the mass market, but I'd prefer something which presumes more mathematical knowledge and is either more concise or better supported.
The basic argument is you should try to falsify your beliefs through texts, try things which will succeed/fail in ways which are independent of mainstream beliefs or the rest of your "portfolio" of ideas and beliefs, etc. One of the key ideas is separating experiments based on the 2 axes of cost of failure and benefit if successful, and to try to take risks/make mistakes/experiment in ways where failure has low cost but high returns if successful.
The good part: it's an introduction to decision theory for people who might actually have real decisions to make (i.e. not just academics studying decision theory...). Lots of practical examples from business, clear presentation, etc.
Downside: Because it can't use normal human language like "local maxima" and mathematical analogies, it's really verbose and imprecise.
Calling likely-to-fail-but-positive-EV experiments "deliberate mistakes" or failures is a stretch, but it's the hook for the book, so he repeats it a lot.
Overall, this is a decent book for the mass market, but I'd prefer something which presumes more mathematical knowledge and is either more concise or better supported.
February 1, 2021
This is an inspiring book that explores how the different types of mistakes can enable development, learning and innovation.
It is well written and the examples of diverse and strong. There is attention to the great scholars and writers - and their mistakes.
Most impressive was the framing of failure - retrospectively.
It is well written and the examples of diverse and strong. There is attention to the great scholars and writers - and their mistakes.
Most impressive was the framing of failure - retrospectively.
November 25, 2025
BLUF (Bottom Line Up Front)
Oscar Wilde said experience is what we call our mistakes.
Schoemaker suggests that if we diversify our mistakes on purpose, the few that pay off will more than cover the rest—experience by design, not accident.
Executive Summary
Brilliant Mistakes argues that smart progress comes from intentional, bounded errors. Schoemaker frames learning as a portfolio of small, varied tests—each probing a different assumption so leaders discover what tidy models overlook.
Key ideas:
• Strategic mistakes: deliberate experiments that reveal hidden variables.
• A portfolio approach: many small bets beat one big, brittle one.
• Tests should be “negatively correlated” so one failure increases the odds another succeeds.
• Overconfidence narrows perception; curiosity widens it.
Review
The financial metaphor of “portfolio thinking” stuck with me: a winning outlier can offset a dozen losses. Instead of avoiding error at all costs, smart individuals and organizations make multiple, deliberate mistakes that are low-cost, reversible, and diversified “bets.” As a learning scientist, that maps perfectly to designing instructional pilots. Running many different tests—not just variations of a theme—helps us surface insights we’d never see otherwise. This doesn’t mean being reckless. As an African proverb warns, “Never test the depth of a river with both feet.” At WGU, keeping “one foot on the bank” while the other explores new assessments or supports keeps the risk tolerable and the learning rich.
This was a solid 3-star read: helpful framing, but sometimes too heavy on business parables and too light on method. I wanted clearer guidance on building a truly diversified experimental portfolio. Still, the core idea reshaped how I think about failure. A good mistake is a sensor in the dark. Place enough sensors, and the path forward becomes easier to see.
Similar Reads
• Antifragile — systems that gain from volatility.
• Black Box Thinking — using failure as structured learning.
• The Signal and the Noise — diversified hypotheses over single forecasts.
Authorship Note: This review was co-authored using a time-saving GPT I built to help structure and refine my thoughts.
Oscar Wilde said experience is what we call our mistakes.
Schoemaker suggests that if we diversify our mistakes on purpose, the few that pay off will more than cover the rest—experience by design, not accident.
Executive Summary
Brilliant Mistakes argues that smart progress comes from intentional, bounded errors. Schoemaker frames learning as a portfolio of small, varied tests—each probing a different assumption so leaders discover what tidy models overlook.
Key ideas:
• Strategic mistakes: deliberate experiments that reveal hidden variables.
• A portfolio approach: many small bets beat one big, brittle one.
• Tests should be “negatively correlated” so one failure increases the odds another succeeds.
• Overconfidence narrows perception; curiosity widens it.
Review
The financial metaphor of “portfolio thinking” stuck with me: a winning outlier can offset a dozen losses. Instead of avoiding error at all costs, smart individuals and organizations make multiple, deliberate mistakes that are low-cost, reversible, and diversified “bets.” As a learning scientist, that maps perfectly to designing instructional pilots. Running many different tests—not just variations of a theme—helps us surface insights we’d never see otherwise. This doesn’t mean being reckless. As an African proverb warns, “Never test the depth of a river with both feet.” At WGU, keeping “one foot on the bank” while the other explores new assessments or supports keeps the risk tolerable and the learning rich.
This was a solid 3-star read: helpful framing, but sometimes too heavy on business parables and too light on method. I wanted clearer guidance on building a truly diversified experimental portfolio. Still, the core idea reshaped how I think about failure. A good mistake is a sensor in the dark. Place enough sensors, and the path forward becomes easier to see.
Similar Reads
• Antifragile — systems that gain from volatility.
• Black Box Thinking — using failure as structured learning.
• The Signal and the Noise — diversified hypotheses over single forecasts.
Authorship Note: This review was co-authored using a time-saving GPT I built to help structure and refine my thoughts.
Read
November 26, 2025In "Brilliant Mistakes: Finding Success on the Far Side of Failure", the central idea is that mistakes are not regrettable detours but essential components of growth, innovation, and long-term success. The author argues that progress rarely follows a perfect path and that people, teams, and entire industries advance precisely because they experiment, miscalculate, and learn from unexpected outcomes. Instead of treating errors as threats, this book encourages readers to see them as signals - clues about what is possible, what needs improvement, and where hidden opportunities live. The narrative begins by challenging the widespread obsession with perfection, which often suffocates creativity and prevents individuals from making bold moves. By shifting our mindset from avoidance to exploration, we free ourselves to push boundaries and discover breakthroughs that would never occur in a risk-free environment.
The author explains that competence isn’t built by avoiding errors but by embracing the uncertainty that creates them. Every new venture, skill, or creative attempt contains unknowns, and it’s unrealistic to expect flawless execution in unfamiliar territory. People often stay trapped in the 'safe zone,' believing that maintaining a spotless track record equals success. But the book makes clear that this mindset limits potential. The world is far too dynamic for risk-free strategies; markets shift, technology evolves, and expectations change. Those who cling to certainty find themselves unprepared when change eventually arrives. Mistakes, on the other hand, force us to adapt. They demand that we reconsider our assumptions, question our habits, and evaluate what is truly working. This process - while uncomfortable - sharpens judgment and builds resilience.
A major theme is that not all mistakes are created equal. Some are sloppy or careless, but many are 'intelligent mistakes,' the kind that arise from thoughtful attempts to learn, innovate, or break into new territory. These intelligent mistakes are the ones that often lead to remarkable insights. The author illustrates that if you never attempt anything uncertain - if you’re always playing by the rules of what worked yesterday - you miss the chance to discover what could work tomorrow. Intelligent mistakes have value because they provide data. They reveal underexplored paths, show what customers actually respond to, expose weaknesses in systems or assumptions, and illuminate possibilities no one noticed before. Instead of punishing these mistakes, the book urges leaders and individuals to reward them, because they are signs of curiosity and courage.
The narrative spends time exploring how organizations can create environments where experimentation feels safe. In many workplaces, the fear of failure is so strong that employees remain silent when they have ideas, or they follow routines even when those routines clearly no longer serve the organization’s goals. This happens not because people lack creativity, but because they feel that any deviation from the plan could harm their reputation. The author suggests that great companies cultivate cultures where people can test ideas on a small scale, evaluate results quickly, and talk openly about what they learned. Instead of celebrating only victories, these environments celebrate transparency, effort, and reflection. When failure becomes a tool rather than a threat, innovation becomes far more accessible.
Another insight is the emotional component of mistakes. People often internalize failure, believing it reflects something flawed about their character or abilities. The book stresses that this emotional weight is what makes mistakes feel so overwhelming. Viewed objectively, a mistake is simply an event - a result that didn’t match expectations. But viewed emotionally, it can feel like a humiliation or personal defeat. Learning to separate identity from outcome is essential. When people no longer believe that a misstep defines them, they become more willing to experiment, take risks, and grow. This emotional detachment doesn’t eliminate responsibility - it enhances it. When mistakes are seen clearly rather than through the haze of self-criticism, it becomes easier to analyze them honestly and extract meaningful lessons.
The book also explores how strategic mistakes often lead to breakthroughs in science, technology, and business. Many of history’s most significant discoveries were unexpected side effects - results no one intended but everyone benefited from. Serendipity favors those who experiment widely enough to stumble upon something new. The author argues that innovation can’t be fully planned; it emerges from exploration. By allowing room for the unpredictable, individuals and organizations position themselves to discover insights that no amount of careful planning could produce. The willingness to wander, to test unconventional ideas, or to approach problems from unfamiliar angles creates openings for unexpected progress.
A recurring message is that reflection is the bridge between a mistake and its value. Errors that are ignored, minimized, or denied cannot produce growth. The author encourages readers to adopt a habit of structured reflection: examining what assumptions were made, what factors were overlooked, what the results indicate, and how the new insights can be applied going forward. Reflection turns confusion into clarity. It prevents repeated errors and transforms random experiences into deliberate knowledge. Without reflection, mistakes become burdens; with reflection, they become assets.
Throughout the book, the author emphasizes that success is not a straight shot forward but a weaving path shaped by bold decisions, misjudgments, and adjustments. Every person who has achieved extraordinary results has accumulated a long list of failed attempts. The difference between those who stagnate and those who progress is not the number of mistakes but the attitude toward them. People who advance are those who remain curious, who are honest enough to confront their missteps, and who are willing to revise their approach rather than cling to outdated strategies. Growth is iterative, and improvement requires taking action even before certainty exists.
The closing chapters encourage readers to integrate mistake-friendly thinking into their everyday lives. This involves practicing small acts of experimentation, embracing imperfect starts, and challenging old assumptions. It means recognizing that perfectionism is not practicality - it’s paralysis. By letting go of the need to get everything right on the first try, individuals free themselves to pursue opportunities that once felt too risky or intimidating. The goal isn’t to seek failure but to accept that failure is an unavoidable companion of big ambitions. Once failure loses its power to intimidate, possibilities expand dramatically.
In the end, "Brilliant Mistakes: Finding Success on the Far Side of Failure" argues that mistakes are not signs of incompetence but evidence of engagement with complex, meaningful challenges. They show that someone is trying, stretching, and pushing into new territory. When viewed through this lens, mistakes become affirmations of progress rather than blemishes to hide. The book concludes by reminding readers that success requires courage - the courage to act without certainty, to learn from what doesn’t work, and to trust that each misstep contains a lesson that moves them closer to mastery. Instead of aspiring to a flawless life, we should aspire to a life rich with exploration, learning, and growth, knowing that mistakes are not obstacles to success but pathways toward it.
The author explains that competence isn’t built by avoiding errors but by embracing the uncertainty that creates them. Every new venture, skill, or creative attempt contains unknowns, and it’s unrealistic to expect flawless execution in unfamiliar territory. People often stay trapped in the 'safe zone,' believing that maintaining a spotless track record equals success. But the book makes clear that this mindset limits potential. The world is far too dynamic for risk-free strategies; markets shift, technology evolves, and expectations change. Those who cling to certainty find themselves unprepared when change eventually arrives. Mistakes, on the other hand, force us to adapt. They demand that we reconsider our assumptions, question our habits, and evaluate what is truly working. This process - while uncomfortable - sharpens judgment and builds resilience.
A major theme is that not all mistakes are created equal. Some are sloppy or careless, but many are 'intelligent mistakes,' the kind that arise from thoughtful attempts to learn, innovate, or break into new territory. These intelligent mistakes are the ones that often lead to remarkable insights. The author illustrates that if you never attempt anything uncertain - if you’re always playing by the rules of what worked yesterday - you miss the chance to discover what could work tomorrow. Intelligent mistakes have value because they provide data. They reveal underexplored paths, show what customers actually respond to, expose weaknesses in systems or assumptions, and illuminate possibilities no one noticed before. Instead of punishing these mistakes, the book urges leaders and individuals to reward them, because they are signs of curiosity and courage.
The narrative spends time exploring how organizations can create environments where experimentation feels safe. In many workplaces, the fear of failure is so strong that employees remain silent when they have ideas, or they follow routines even when those routines clearly no longer serve the organization’s goals. This happens not because people lack creativity, but because they feel that any deviation from the plan could harm their reputation. The author suggests that great companies cultivate cultures where people can test ideas on a small scale, evaluate results quickly, and talk openly about what they learned. Instead of celebrating only victories, these environments celebrate transparency, effort, and reflection. When failure becomes a tool rather than a threat, innovation becomes far more accessible.
Another insight is the emotional component of mistakes. People often internalize failure, believing it reflects something flawed about their character or abilities. The book stresses that this emotional weight is what makes mistakes feel so overwhelming. Viewed objectively, a mistake is simply an event - a result that didn’t match expectations. But viewed emotionally, it can feel like a humiliation or personal defeat. Learning to separate identity from outcome is essential. When people no longer believe that a misstep defines them, they become more willing to experiment, take risks, and grow. This emotional detachment doesn’t eliminate responsibility - it enhances it. When mistakes are seen clearly rather than through the haze of self-criticism, it becomes easier to analyze them honestly and extract meaningful lessons.
The book also explores how strategic mistakes often lead to breakthroughs in science, technology, and business. Many of history’s most significant discoveries were unexpected side effects - results no one intended but everyone benefited from. Serendipity favors those who experiment widely enough to stumble upon something new. The author argues that innovation can’t be fully planned; it emerges from exploration. By allowing room for the unpredictable, individuals and organizations position themselves to discover insights that no amount of careful planning could produce. The willingness to wander, to test unconventional ideas, or to approach problems from unfamiliar angles creates openings for unexpected progress.
A recurring message is that reflection is the bridge between a mistake and its value. Errors that are ignored, minimized, or denied cannot produce growth. The author encourages readers to adopt a habit of structured reflection: examining what assumptions were made, what factors were overlooked, what the results indicate, and how the new insights can be applied going forward. Reflection turns confusion into clarity. It prevents repeated errors and transforms random experiences into deliberate knowledge. Without reflection, mistakes become burdens; with reflection, they become assets.
Throughout the book, the author emphasizes that success is not a straight shot forward but a weaving path shaped by bold decisions, misjudgments, and adjustments. Every person who has achieved extraordinary results has accumulated a long list of failed attempts. The difference between those who stagnate and those who progress is not the number of mistakes but the attitude toward them. People who advance are those who remain curious, who are honest enough to confront their missteps, and who are willing to revise their approach rather than cling to outdated strategies. Growth is iterative, and improvement requires taking action even before certainty exists.
The closing chapters encourage readers to integrate mistake-friendly thinking into their everyday lives. This involves practicing small acts of experimentation, embracing imperfect starts, and challenging old assumptions. It means recognizing that perfectionism is not practicality - it’s paralysis. By letting go of the need to get everything right on the first try, individuals free themselves to pursue opportunities that once felt too risky or intimidating. The goal isn’t to seek failure but to accept that failure is an unavoidable companion of big ambitions. Once failure loses its power to intimidate, possibilities expand dramatically.
In the end, "Brilliant Mistakes: Finding Success on the Far Side of Failure" argues that mistakes are not signs of incompetence but evidence of engagement with complex, meaningful challenges. They show that someone is trying, stretching, and pushing into new territory. When viewed through this lens, mistakes become affirmations of progress rather than blemishes to hide. The book concludes by reminding readers that success requires courage - the courage to act without certainty, to learn from what doesn’t work, and to trust that each misstep contains a lesson that moves them closer to mastery. Instead of aspiring to a flawless life, we should aspire to a life rich with exploration, learning, and growth, knowing that mistakes are not obstacles to success but pathways toward it.
January 3, 2022
I think this book was misleadingly named. Sure, it talks about mistakes which are true mistakes, but it is really about taking reasonable risks. Be adventuresome, but be smart about the ventures that you undertake. You can trust your gut, but have a net.
While I did enjoy this book, it was not any brilliant revelation. Just some good sense.
I listened to the audio version of this book. It was well narrated.
While I did enjoy this book, it was not any brilliant revelation. Just some good sense.
I listened to the audio version of this book. It was well narrated.
June 8, 2021
"An open mind is a fertile mind" - Paul J.H. Shoemaker
This is a book that doesn't tell us anything new. We learn from mistakes and we must allow for our organizations and personal lives to have room for mistakes that can give us insights and change the way we think about things.
With an interesting storytelling about diverse famous people and organizations (such as Fleming and Google) making brilliant mistakes, Paul gifts us an interesting framework to use at the time of making mistakes. This framework might seem obvious in hindsight, but it actually shares some light on the reason why some mistakes are acceptable and some are not.
This is a book that doesn't tell us anything new. We learn from mistakes and we must allow for our organizations and personal lives to have room for mistakes that can give us insights and change the way we think about things.
With an interesting storytelling about diverse famous people and organizations (such as Fleming and Google) making brilliant mistakes, Paul gifts us an interesting framework to use at the time of making mistakes. This framework might seem obvious in hindsight, but it actually shares some light on the reason why some mistakes are acceptable and some are not.
November 24, 2017
Um bom livro para incentivá-lo a tentar :-)
Alguns exemplos de erros notáveis, de pessoas capazes aprender com seus equívocos e não paenas ficar lamentando-os.
Errar significa ser capaz de arriscar, de erguer-se após a queda, de melhora cada vez mais.
Ao final apêndices, notas explicativas e índice.
Pena o livro ser tão curto !
Alguns exemplos de erros notáveis, de pessoas capazes aprender com seus equívocos e não paenas ficar lamentando-os.
Errar significa ser capaz de arriscar, de erguer-se após a queda, de melhora cada vez mais.
Ao final apêndices, notas explicativas e índice.
Pena o livro ser tão curto !
June 5, 2019
Solid concept and, likely, a convincing approach to framing experimentation in a corporate environment.
November 25, 2025
write down the thought Process of decision, quality of decision matter. after the outcome think back to the reasons and arguments and evaluate based on that
November 29, 2025
liked the approach. little light. It reminded me of the awesome website called autopsy dissecting startups downfalls.
April 2, 2015
The premise of the book is that mistakes are the portals to discovery. E.g. discovery of penicillin by Alexander Fleming; invention of light bulb by Thomas Edison; or flight by the Wright Brothers. Where, it was argued, that either conventional wisdom was that it could not be done (such as human flight), or some form of sloppiness (out of the norm) led to the discovery (like penicillin, or for that matter, saccharin), or just dogged determination despite multiple failures (like the light bulb). Ok, I can accept that. Except that I wouldn't classify some of them as mistakes though I accept that staying within a comfort zone is unlikely to lead to any amazing discoveries; and to make discoveries, and push the boundaries, one must accept mistakes along the way.
A so-so read.
A so-so read.
October 20, 2011
Absolutely fascinating read. Again, another quality Wharton Digital Press Publication that I received from Netgalley and read in one day. This book had alot more other data to absorb, so this will be a book I purchase and mark up.
Information in this book was discussed in business school, but I thought the author did an excellent job of laying it out, discussing it and offered fantastic examples. I could see this book used in everything from new ventures to organizational development.
Information in this book was discussed in business school, but I thought the author did an excellent job of laying it out, discussing it and offered fantastic examples. I could see this book used in everything from new ventures to organizational development.
March 17, 2015
As someone who lives in fear of failure, I liked this book as a way to get me to think about mistakes from another angle. The author does a good job of keeping what could become dry material interesting through the use of stories and examples. The book can take some technical swings into economic and business theory but I was able to follow without a problem and I got a few strategies to test out the next time a mistake comes up at work (I'll work up to the deliberate mistakes as I go).
July 25, 2016
Fail harder. Fail better. What does that actually mean? The author shows that making mistakes can be good for both people and companies. The mistakes he's talking about are more experiments than mistakes. The book is about not allowing fear of failure to shut down attempts and he makes the very good point that companies should reward both effort and results. He gives plenty of good examples from history and really shows how being comfortable with failure is a key component of success.
January 14, 2014
Wonderful insights and overlooked wisdom delivered in this book, but it would have been so much better if he went more in-depth about the process of making brilliant mistakes. Those who know about all the serendipitous inventions won't be introduced to anything new here except the process of making brilliant mistakes.
Maybe he'll write a book dedicated to the process next, I'd buy it.
Maybe he'll write a book dedicated to the process next, I'd buy it.
March 30, 2012
When I started reading it I thought I made a wrong choice picking this book or that I will totally disagree with it, I still think it's too focused on the word mistake/error but I actually like the content.
March 30, 2013
This is one great read about 'Why minimizing mistakes might be a huge mistake' and how brilliance can be found in each and every mistake. Highly recommended.
July 6, 2013
Very good approach to decision making
Displaying 1 - 18 of 18 reviews